Norbornene derivative and norbornene polymer obtained therefrom through ring opening polymerization

a technology of norbornene and derivative, applied in the field of norbornene derivative, can solve the problems of heat resistance and water resistance, optical characteristics of the generated optical product also failed to meet the demands, etc., and achieve excellent transparency, improved light resistance, and improved workability

Inactive Publication Date: 2004-12-02
JSR CORPORATIOON
View PDF5 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

0279] A variety of known additives can be added to a ring opening polymer of the present invention or a hydrogenated product thereof. Examples of such additives include phenol-based or hydroquinone-based antioxidants such as 2,6-di-t-butyl-4-methylphenol, 2,2-methylenebis(4-ethyl-6-t-butyl-phenol), 2,5-di-t-butylhydroquinone, tetrakis[methylene-3-(3,5-di-t-butyl--4-hydroxyphenyl)propionate]methane, 4,4-thiobis-(6-t-butyl-3methylphenol), 1,4-bis(4-hydroxyphenyl)cyclohexane and octadecyl-3-(3,5-di-t-butyl-4-hyd-roxyphenyl)propionate, as well as phosphorus-based antioxidants such as tris(4-methoxy-3,5-diphenyl)phosphite, tris(nonylphenyl)phosphite and tris(2,4-di-t-butylphenyl)phosphite, and by adding either one, or two or more of these antioxidants, the oxidation stability of the ring opening polymer or the hydrogenated product thereof can be improved. In addition, by adding ultraviolet absorbing agents such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone and 2,2-methylenebis[4-(1,1,3,3-tetrameth-ylbutyl)-6-[(2H-benzotriazol-2-yl)phenol]], the light res...

Problems solved by technology

However, although acrylic-based resins offer excellent transparency, they have problems in terms of heat resistance and water resistance.
In contrast, polycarbonate-based resins offer superior performance to acrylic resins in terms of heat resistance and water resistance, but suffer from different problems such as a high birefringence.
Cyclic olefin-based polymers such as those described above are typically converted to pr...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Norbornene derivative and norbornene polymer obtained therefrom through ring opening polymerization
  • Norbornene derivative and norbornene polymer obtained therefrom through ring opening polymerization
  • Norbornene derivative and norbornene polymer obtained therefrom through ring opening polymerization

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 5-(4-biphenylcarbonyloxy)bicyclo[2.2.1]hept-2-ene

[0291] 17

[0292] 28 g (253.9 mmol) of norbornene alcohol (endo form / exo form molar ratio of 8 / 1) was measured into a 500 mL flask equipped with a dropping funnel, and the air in the system was replace with nitrogen. 41 mL (507.8 mmol) of pyridine was then added dropwise, and stirred well with a stirrer to dissolve the pyridine. Subsequently, with the temperature of the reaction system maintained at 4.+-.2.degree. C. using an ice bath, and with adequate stirring, 50 g (230.8 mmol) of 4-phenylbenzoyl chloride dissolved in 200 mL of THF (tetrahydrofuran) was gradually added dropwise. Following completion of this dropwise addition, stirring was continued for 1 hour with the reaction system still in the ice bath, and then for a further 1 hour at room temperature, and finally the reaction system was refluxed for 30 minutes. Following cooling to room temperature, the generated pyridine salts were removed by filtration, and the re...

example 2

Synthesis of 5-(2-naphthalenecarbonyloxy)bicyclo[2.2.1]hept-2-ene

[0296] 18

[0297] With the exceptions of using 44 g (230.8 mmol) of 2-naphthoyl chloride instead of 4-phenylbenzoyl chloride, and purifying the reactants using a column (filler: Al.sub.2O.sub.3, developing solvent: hexane), reaction in the same manner as the example 1 yielded 46 g of a white solid of 5-(2-naphthalenecarbonyloxy)bicyclo[2.2.1]hept-2-ene. Analysis of the product monomer by HPLC revealed a purity of 99%.

[0298] Analysis of the .sup.1H-NMR spectrum in the same manner as described above for the example 1 revealed a stereoisomeric ratio (the endo type / exo type molar ratio) for the substituent group within the monomer of 8 / 1. Furthermore, in the infrared absorption (IR) spectrum, the stretching vibration absorption for the CH groups of the aromatic rings was observed within the vicinity of 3050 cm.sup.-1, and the stretching vibration absorption for the CO group within the ester carbonyl group was observed within...

example 3

Synthesis of 5-(1-naphthalenecarbonyloxy)bicyclo[2.2.1]hept-2-ene

[0300] 19

[0301] With the exception of using 44 g (230.8 mmol) of 1-naphthoyl chloride instead of 2-naphthoyl chloride, reaction in the same manner as the example 2 yielded 43.8 g of a transparent liquid of 5-(1-naphthalenecarbonyloxy)bicyclo[2.2.1]hept-2-ene. Analysis of the product monomer by HPLC revealed a purity of 98%.

[0302] Analysis of the .sup.1H-NMR spectrum in the same manner as described above for the example 1 revealed a stereoisomeric ratio (the endo type / exo type molar ratio) for the substituent group within the monomer of 8 / 1. Furthermore, in the infrared absorption (IR) spectrum, the stretching vibration absorption for the CH groups of the aromatic rings was observed within the vicinity of 3050 cm.sup.-1, and the stretching vibration absorption for the CO group within the ester carbonyl group was observed within the vicinity of 1710 to 1730 cm.sup.-1.

[0303] The .sup.1H-NMR spectrum and the infrared absor...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Lengthaaaaaaaaaa
Percent by massaaaaaaaaaa
Lengthaaaaaaaaaa
Login to view more

Abstract

A novel norbornene derivative represented by a general formula (1m) shown below is provided. By conducting a ring opening polymerization of this norbornene derivative, or by performing a subsequent hydrogenation following the ring opening polymerization, a ring opening polymer or a hydrogenated product thereof with an excellent low birefringence can be obtained. [wherein, at least one of R<1 >to R<4 >is a group selected from the group consisting of groups represented by a general formula (1-1) shown below and groups represented by a general formula (1-2) shown below] [wherein, at least one of R, Rand Z is a group represented by the formula -C(O)O-].

Description

[0001] The present invention relates to a precursor monomer compound for a cyclic olefin-based polymer which combines excellent transparency and a low birefringence.[0002] In addition, the present invention relates to a norbornene-based ring opening polymer which combines excellent transparency and a low birefringence.[0003] Conventionally, transparent resins are used as the materials for molded products which typically require transparency such as automobile components, illumination equipment and electrical components. Particularly in recent years, the application of these resins as optical materials, in which the optical properties are important, continues to progress. Examples of known transparent resins which can be ideally applied to such applications include polycarbonate-based resins and acrylic-based resins. However, although acrylic-based resins offer excellent transparency, they have problems in terms of heat resistance and water resistance. In contrast, polycarbonate-base...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C69/00C08G61/06C08G61/08
CPCC07C69/753C07C69/76C07C2102/42C07C2103/18C07C2103/24C07C2103/86C08G61/06C08G61/08C07C2602/42C07C2603/18C07C2603/24C07C2603/86
Inventor MIYAKI, NOBUYUKIMIYAMOTO, YOSHIKAZUFUKUHARA, SEIJIOOTSUKI, TOSHIHIRO
Owner JSR CORPORATIOON
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap